3. Britney Spears & Kevin Federline
In one of the most infamous Hollywood romance stories ever, pop icon Britney Spears fell for backup dancer Kevin Federline, in early 2004 and got engaged after dating 90 days! That would have been great news under normal circumstances, but everyone quickly realized that Federline was also involved with Moesha actress and mother of his two kids, Shar Jackson.
Despite tremendous controversy and warnings from friends and family, Britney tied the knot in a surprise ceremony with Federline on October 6, 2004. The married couple had two back-to-back kids in a short time frame, but predictions of a tumultuous relationship came true as Kevin suffered through a failed rap career and both were heavily criticized for their bad parenting and nightclub antics. Within a few years, their relationship had completely deteriorated, ending with a bizarre divorce in 2007 sent through text and fax messages. A wicked custody battle and mental health issues for Spears followed as the two went from lovers to enemies. But throughout the highs and lows, an agreement was reached and the two have been able to co-parent for their children.
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